Enzyme-catalysed approach to the preparation of triazole antifungals: synthesis of (−)-genaconazole

Acetti, Daniela; Brenna, Elisabetta; Fuganti, Claudio; Gatti, Francesco G.; Serra, Stefano

doi:10.1016/j.tetasy.2009.09.024

Cited by 30 publications

(11 citation statements)

References 17 publications

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“…For example, the enantioenriched 2 p could be a useful compound for the synthesis of the natural product tanikolide 17. In addition, the 2,4‐difluorophenyl‐substituted 2 j is an important chiral building block for the preparation of triazole antifungal agents18 such as Genaconazole, Ravuconazole, and Albaconazole.…”

Section: Optimization Studies[a]mentioning

confidence: 99%

Mild One‐Step Synthesis of 4,6‐Benzylideneglycopyranosides from Aromatic Aldehydes and Gelation Abilities of the Glucose Derivatives

et al. 2015

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We report herein an efficient one‐step synthesis of 4,6‐benzylidene glycoside derivatives from aromatic aldehydes bearing electron‐donating or ‐withdrawing groups as well as polymerisable monomer groups. Glucose, mannose and galactose derivatives could also be used successfully. Several of the glucose derivatives thus obtained acted as gelators for various solvents, including water. 4‐(n‐Butoxybenzylidene)glucose derivative 3a produced both a clear squalane gel and a hydrogel at 0.1 wt.‐%. Furthermore, 3‐(n‐butoxybenzylidene)glucose derivative 3i produced a clear organogel and an opaque hydrogel. The critical gelation concentration (CGC) of 3i in squalane was determined to be 0.02 wt.‐%, which is one of the lowest CGC values reported so far. The organogels, hydrogels and aqueous solution gels produced from 3a and 3d exhibited thixotropy. The strength and thixotropy of the organo‐ and hydrogel produced from 3a were estimated by a rheometer. The gel morphologies were observed by field‐emission and wet‐scanning electron microscopy, and the self‐assembly modes were analysed by XRD. We have concluded that super‐gelators can be created by this method.

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Section: Optimization Studies[a]mentioning

confidence: 99%

Mild One‐Step Synthesis of 4,6‐Benzylideneglycopyranosides from Aromatic Aldehydes and Gelation Abilities of the Glucose Derivatives

et al. 2015

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“…For example, the enantioenriched 2 p could be a useful compound for the synthesis of the natural product tanikolide. [17] In addition, the 2,4-difluorophenyl-substituted 2 j is an important chiral building block for the preparation of triazole antifungal agents [18] such as Genaconazole, Ravuconazole, and Albaconazole.…”

Section: Methodsmentioning

confidence: 99%

Palladium‐Catalyzed Decarboxylative Cycloaddition of Vinylethylene Carbonates with Formaldehyde: Enantioselective Construction of Tertiary Vinylglycols

et al. 2014

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An efficient method for the enantioselective construction of tertiary vinylglycols through a palladium-catalyzed asymmetric decarboxylative cycloaddition of vinylethylene carbonates with formaldehyde was developed. By using a palladium complex generated in situ from [Pd 2 -(dba) 3 ]·CHCl 3 and a phosphoramidite ligand as a catalyst under mild reaction conditions, the process allows conversion of racemic 4-substituted 4-vinyl-1,3-dioxolan-2-ones into the corresponding 1,3-dioxolanes, as methylene acetal protected tertiary vinylglycols, in high yields with good to excellent enantioselectivities.

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“…Second, it was shown that polyfluorophenyl oxiranes are excellent substrates for S N Ar reactions [9] (Scheme 4). Thus, 2 l underwent an efficient substitution reaction with piperidine and sodium methylthiolate to produce the corresponding N-and S-containing products 5 a and 5 b, respectively, in excellent yields and with no oxirane ring-opening [10] products detected.…”

Section: Methodsmentioning

confidence: 99%

“…NaHMDS = sodium hexamethyldisilazide. ketones 1 i,j and N-tosylindole-3-yl ketone 1 k, were converted into the corresponding epoxides 2 i-k in good yields (entries [9][10][11]. Importantly, in contrast to the epoxidation reaction with alkynyl bromides [4] and cyanogen bromide, [5] PFPBr smoothly reacted with propiophenone 1 l and butyrophenone 1 m, producing the corresponding trisubstituted oxiranes 2 l,m in good yields and very high diastereoselectivities [7] (entries 12 and 13).…”

mentioning

confidence: 99%

One‐Pot Arylative Epoxidation of Ketones by Employing Amphoteric Bromoperfluoroarenes

Zhou

Gevorgyan

2011

Angew Chem Int Ed

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Enzyme-catalysed approach to the preparation of triazole antifungals: synthesis of (−)-genaconazole

Cited by 30 publications

References 17 publications

Mild One‐Step Synthesis of 4,6‐Benzylideneglycopyranosides from Aromatic Aldehydes and Gelation Abilities of the Glucose Derivatives

Mild One‐Step Synthesis of 4,6‐Benzylideneglycopyranosides from Aromatic Aldehydes and Gelation Abilities of the Glucose Derivatives

Palladium‐Catalyzed Decarboxylative Cycloaddition of Vinylethylene Carbonates with Formaldehyde: Enantioselective Construction of Tertiary Vinylglycols

One‐Pot Arylative Epoxidation of Ketones by Employing Amphoteric Bromoperfluoroarenes

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